Fenchone

Fenchone is an organic compound classified as a monoterpenoid and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to those of camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery.

Fenchone
Names
IUPAC name
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
Other names
1,3,3-Trimethyl-2-norcamphanone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.458
KEGG
PubChem CID
UNII
  • InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3 Y
    Key: LHXDLQBQYFFVNW-UHFFFAOYSA-N Y
  • InChI=1/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
    Key: LHXDLQBQYFFVNW-UHFFFAOYAX
SMILES
  • O=C1C(C)(C)C2CC1(C)CC2
Properties
C10H16O
Molar mass 152.23 g/mol
Density 0.948 g/cm3
Melting point 6.1 °C (43.0 °F; 279.2 K)
Boiling point 193.5 °C (380.3 °F; 466.6 K)
Refractive index (nD)
 1.4625
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Other names for fenchone include dl-fenchone and (±)-fenchone. It is a mixture of the enantiomers d-fenchone and l-fenchone. Other names for d-fenchone include (+)-fenchone and (1S,4R)-fenchone. Other names for l-fenchone include (−)-fenchone and (1R,4S)-fenchone. The d-fenchone enantiomer occurs in pure form in wild, bitter and sweet fennel plants and seeds, whereas the l-fenchone enantiomer occurs in pure form in wormwood, tansy, and cedarleaf.

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